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(1) Provide names for compounds A, B, C below. OH H2SO4 H2O, heat B c A A: B: C: Can compounds B and c be differentiated by 3H NMR? Explain. Consider integration, coupling (signal splitting patterns), and coupling constants. If your lecture did not cover coupling constants, mention that in your answer. (2) What are typical IR frequencies observed for an: (a) alcohol: (b) amine: (c) ketone (d) carboxylic acid (e) alkyne (f) alkene (3) Predict how many proton and carbon MR signals there will be for the following compounds: o NO2 OH N CI CH3 OH o HO o CI CI O2N NO2 o paracetamol trichlorophenol (TCP) trinitrotoluene (TNT) aspirin antiseptic ¹H signals: # 1H signals: # 1H signals: # ¹H signals: 1°c signals: 13c signals: # 13c signals: # 11c signals: (4) Predict the splitting patterns for the indicated hydrogens for putrescine and cadaverine. (e.g. s, d.t. q. dd, dt, etc.) a a NH2 c H2N H2N NH2 b b Putrescine: (a) (b) Cadaverine: (a) (b) (c) (5) Can the two allylic sulfur compounds from "eau de skunk" be differentiated by proton NMR? Explain the differences you'd expect to see for the two spectra. Consider integration too. SH SH (6) Can proton and carbon NMR distinguish the compounds below? Explain. OH o o black truffle smell HO raspberry ketone rose smell (diluted) grapefruit smell (7) OH o N o isooctane OH HO BHT indigo (dye) o (antioxidant: food) 1H signals: # 1H signals: # 1H signals: # 1H signals: 13c signals: "c signals: # 10c signals: # # 1°C signals:

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1. A : 2-methyl-2-buthanol B: 2-methyl-butene C: 2-methyl-2-butene
These two compounds can be differentiated because in the first case methyl group from the end of chain would split CH2 proton signal into four, and CH3 would have three peaks, because of the double bond then there would be no splitting for =CH2 and CH3. In the second example two CH3 groups would have one signal because of the symmetry...

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